Domanda del libro di testo
What product is obtained from the reaction of excess benzene with each of the following reagents?
c. dichloromethane + AlCl3
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Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 48c
Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 48cCapitolo 18, Problema 48c
Draw the product(s) of each of the following reactions:
c. p-xylene + acetyl chloride + AlCl3 followed by H2O
Guida verificata passo dopo passo1
Step 1: For part (c), recognize that the reaction involves Friedel-Crafts acylation. This reaction uses acetyl chloride (CH3COCl) and AlCl3 as a Lewis acid catalyst to introduce an acyl group (-COCH3) onto an aromatic ring. p-Xylene (1,4-dimethylbenzene) is the aromatic compound in this case.
Step 2: Identify the positions on the aromatic ring where substitution is likely to occur. The methyl groups on p-xylene are electron-donating groups, which activate the aromatic ring and direct substitution to the ortho and para positions relative to themselves. Since the para position is already occupied, the acyl group will be introduced at one of the ortho positions relative to a methyl group.
Step 3: Write the intermediate formed after the acylation step. The acyl group attaches to one of the ortho positions, and the AlCl3 catalyst temporarily forms a complex with the aromatic ring. After hydrolysis (H2O step), the catalyst is regenerated, and the final product is obtained.
Step 4: For part (d), recognize that the reaction involves electrophilic aromatic substitution between o-methylaniline (an aromatic amine with a methyl group ortho to the amino group) and benzenediazonium chloride (C6H5N2+Cl−). This is an example of an azo coupling reaction, which forms an azo compound (-N=N-).
Step 5: Determine the site of coupling on o-methylaniline. The amino group (-NH2) is an electron-donating group, activating the aromatic ring and directing substitution to the ortho and para positions relative to itself. Since the ortho position is already occupied by a methyl group, the coupling occurs at the para position. The product is an azo compound where the diazonium group (-N=N-) is attached to the para position of o-methylaniline.
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Friedel-Crafts Acylation
Friedel-Crafts acylation is a reaction that introduces an acyl group into an aromatic ring using an acyl chloride and a Lewis acid catalyst, such as AlCl3. In this process, the aromatic compound (like p-xylene) reacts with the acyl chloride to form a ketone, which retains the aromaticity of the ring. The reaction is important for synthesizing aromatic ketones and understanding electrophilic aromatic substitution.
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Friedel-Crafts Acylation
Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process preserves the aromaticity of the compound and is crucial for modifying aromatic systems. The nature of the substituents on the ring can influence the reactivity and orientation of the substitution, making it essential to consider when predicting products.
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03:07EAS Review
Diazonium Salts
Diazonium salts are highly reactive intermediates formed from primary aromatic amines and nitrous acid. They are key in various coupling reactions, particularly in the synthesis of azo compounds. In the presence of nucleophiles, such as phenols or other aromatic compounds, diazonium salts can undergo electrophilic substitution, leading to the formation of colored azo dyes, which are significant in both organic synthesis and industrial applications.
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Percorso guidato
4:54Review of Nitriles Example 5
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